In the title compound, C
16H
15N
5·4H
2O, the two independent molecules of the asymmetric unit are linked into a three-dimensional structure by a combination of classical hydrogen bonds, C—H
π and aromatic π–π interactions.
Supporting information
CCDC reference: 621512
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.008 Å
- R factor = 0.068
- wR factor = 0.160
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C1 - C6 .. 9.29 su
PLAT417_ALERT_2_B Short Inter D-H..H-D H1 .. H4B .. 1.44 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H1B .. H6B .. 1.29 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H2A .. H6A .. 1.67 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H3A .. H4A .. 2.09 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H5B .. H10 .. 1.63 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT128_ALERT_4_C Non-standard setting of Space group Pca21 .... Pbc21
PLAT230_ALERT_2_C Hirshfeld Test Diff for N8 - C26 .. 5.09 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C24 .. 6.90 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.00
From the CIF: _reflns_number_total 3608
Count of symmetry unique reflns 3615
Completeness (_total/calc) 99.81%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
6 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
Bis(benzimidazol-2-ylmethyl)amine tetrahydrate
top
Crystal data top
C16H15N5·4H2O | F(000) = 1488 |
Mr = 349.39 | Dx = 1.286 Mg m−3 |
Orthorhombic, Pbc21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2b | Cell parameters from 6949 reflections |
a = 4.7111 (6) Å | θ = 2.6–23.4° |
b = 24.857 (3) Å | µ = 0.09 mm−1 |
c = 30.823 (4) Å | T = 292 K |
V = 3609.5 (8) Å3 | Block, yellow |
Z = 8 | 0.40 × 0.20 × 0.06 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3608 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 3171 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −5→5 |
Tmin = 0.963, Tmax = 0.994 | k = −30→28 |
25072 measured reflections | l = −38→38 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0776P)2 + 1.7967P] where P = (Fo2 + 2Fc2)/3 |
3608 reflections | (Δ/σ)max = 0.005 |
451 parameters | Δρmax = 0.33 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 1.0059 (9) | 0.7488 (2) | 0.8491 (2) | 0.0328 (15) | |
C2 | 1.1384 (13) | 0.7939 (2) | 0.8322 (2) | 0.0443 (14) | |
H2 | 1.0914 | 0.8078 | 0.8051 | 0.053* | |
C3 | 1.3433 (13) | 0.8168 (2) | 0.8578 (2) | 0.0482 (15) | |
H3 | 1.4341 | 0.8476 | 0.8478 | 0.058* | |
C4 | 1.4224 (14) | 0.7963 (2) | 0.8981 (2) | 0.0458 (14) | |
H4 | 1.5682 | 0.8124 | 0.9137 | 0.055* | |
C5 | 1.2820 (12) | 0.7513 (3) | 0.9150 (2) | 0.0461 (14) | |
H5 | 1.3301 | 0.7378 | 0.9421 | 0.055* | |
C6 | 1.0681 (12) | 0.7271 (2) | 0.89030 (16) | 0.0298 (11) | |
C7 | 0.7444 (10) | 0.67620 (19) | 0.86279 (15) | 0.0294 (10) | |
C8 | 0.5348 (10) | 0.6335 (2) | 0.8539 (2) | 0.0300 (12) | |
H8A | 0.3788 | 0.6481 | 0.8371 | 0.036* | |
H8B | 0.4588 | 0.6200 | 0.8811 | 0.036* | |
C9 | 0.8191 (11) | 0.5505 (2) | 0.85801 (18) | 0.0367 (12) | |
H9A | 0.9462 | 0.5702 | 0.8770 | 0.044* | |
H9B | 0.9340 | 0.5269 | 0.8401 | 0.044* | |
C10 | 0.6259 (11) | 0.5169 (2) | 0.88515 (17) | 0.0328 (11) | |
C11 | 0.3109 (10) | 0.45932 (19) | 0.90504 (16) | 0.0298 (10) | |
C12 | 0.1107 (12) | 0.4185 (2) | 0.90736 (19) | 0.0418 (13) | |
H12 | 0.0556 | 0.3989 | 0.8831 | 0.050* | |
C13 | −0.0029 (14) | 0.4087 (3) | 0.9484 (3) | 0.0490 (18) | |
H13 | −0.1325 | 0.3807 | 0.9516 | 0.059* | |
C14 | 0.0658 (15) | 0.4374 (3) | 0.9832 (2) | 0.0542 (18) | |
H14 | −0.0257 | 0.4298 | 1.0092 | 0.065* | |
C15 | 0.2640 (14) | 0.4777 (3) | 0.98275 (18) | 0.0503 (15) | |
H15 | 0.3136 | 0.4967 | 1.0076 | 0.060* | |
C16 | 0.3866 (11) | 0.4883 (2) | 0.94235 (17) | 0.0345 (12) | |
C17 | 0.0482 (13) | 0.8820 (3) | 0.6468 (2) | 0.0405 (14) | |
H17A | −0.1090 | 0.8951 | 0.6641 | 0.049* | |
H17B | −0.0280 | 0.8691 | 0.6195 | 0.049* | |
C18 | 0.2482 (10) | 0.9268 (2) | 0.63827 (16) | 0.0323 (11) | |
C19 | 0.5003 (11) | 0.9986 (3) | 0.65140 (17) | 0.0351 (15) | |
C20 | 0.6237 (13) | 1.0457 (2) | 0.6668 (2) | 0.0433 (13) | |
H20 | 0.5680 | 1.0607 | 0.6931 | 0.052* | |
C21 | 0.8295 (13) | 1.0690 (2) | 0.6420 (2) | 0.0501 (15) | |
H21 | 0.9203 | 1.0999 | 0.6518 | 0.060* | |
C22 | 0.9059 (13) | 1.0466 (3) | 0.6015 (2) | 0.0499 (16) | |
H22 | 1.0460 | 1.0632 | 0.5851 | 0.060* | |
C23 | 0.7794 (11) | 1.0012 (2) | 0.58610 (18) | 0.0400 (12) | |
H23 | 0.8294 | 0.9870 | 0.5593 | 0.048* | |
C24 | 0.5740 (11) | 0.9770 (2) | 0.61157 (18) | 0.0314 (12) | |
C25 | 0.3440 (11) | 0.8009 (2) | 0.64126 (19) | 0.0385 (12) | |
H25A | 0.4601 | 0.7774 | 0.6590 | 0.046* | |
H25B | 0.4696 | 0.8216 | 0.6227 | 0.046* | |
C26 | 0.1506 (10) | 0.7674 (2) | 0.61355 (17) | 0.0317 (11) | |
C27 | −0.1619 (10) | 0.70960 (18) | 0.59437 (15) | 0.0278 (10) | |
C28 | −0.3617 (11) | 0.6687 (2) | 0.59237 (19) | 0.0381 (12) | |
H28 | −0.4064 | 0.6488 | 0.6170 | 0.046* | |
C29 | −0.4906 (12) | 0.6581 (3) | 0.5543 (3) | 0.0437 (17) | |
H29 | −0.6278 | 0.6313 | 0.5529 | 0.052* | |
C30 | −0.4201 (14) | 0.6874 (3) | 0.5159 (2) | 0.0500 (16) | |
H30 | −0.5043 | 0.6783 | 0.4896 | 0.060* | |
C31 | −0.2264 (12) | 0.7294 (2) | 0.51769 (19) | 0.0433 (13) | |
H31 | −0.1836 | 0.7496 | 0.4932 | 0.052* | |
C32 | −0.0971 (11) | 0.7403 (2) | 0.55773 (16) | 0.0305 (11) | |
O1 | 0.4748 (9) | 0.44309 (19) | 0.78393 (14) | 0.0493 (12) | |
H1A | 0.6230 | 0.4585 | 0.7769 | 0.074* | |
H1B | 0.3425 | 0.4645 | 0.7846 | 0.074* | |
O2 | 0.0888 (11) | 0.59640 (18) | 0.76511 (17) | 0.0632 (13) | |
H2A | −0.0487 | 0.5875 | 0.7501 | 0.095* | |
H2B | 0.1511 | 0.6254 | 0.7563 | 0.095* | |
O3 | 0.0683 (11) | 0.6945 (2) | 0.71456 (17) | 0.0601 (13) | |
H3A | −0.0586 | 0.6966 | 0.7329 | 0.090* | |
H3B | 0.0014 | 0.6999 | 0.6902 | 0.090* | |
O4 | 0.5653 (10) | 0.7357 (2) | 0.75034 (19) | 0.0648 (14) | |
H4A | 0.6760 | 0.7613 | 0.7479 | 0.097* | |
H4B | 0.5195 | 0.7317 | 0.7756 | 0.097* | |
O5 | 0.6104 (10) | 0.84591 (19) | 0.73494 (16) | 0.0613 (12) | |
H5B | 0.4793 | 0.8477 | 0.7171 | 0.092* | |
H5C | 0.5774 | 0.8669 | 0.7551 | 0.092* | |
O6 | −0.0209 (9) | 0.48752 (18) | 0.74986 (15) | 0.0435 (10) | |
H6A | −0.0152 | 0.5205 | 0.7489 | 0.065* | |
H6B | 0.1256 | 0.4757 | 0.7608 | 0.065* | |
O7 | 0.8412 (8) | 0.61756 (16) | 0.97301 (12) | 0.0461 (10) | |
H7A | 0.9666 | 0.6215 | 0.9914 | 0.069* | |
H7B | 0.8745 | 0.6368 | 0.9519 | 0.069* | |
O8 | 0.3434 (8) | 0.86930 (16) | 0.52654 (12) | 0.0455 (9) | |
H8C | 0.3281 | 0.8936 | 0.5445 | 0.068* | |
H8D | 0.5047 | 0.8691 | 0.5162 | 0.068* | |
N1 | 0.7999 (9) | 0.71513 (16) | 0.83295 (13) | 0.0345 (10) | |
H1 | 0.7230 | 0.7154 | 0.8077 | 0.041* | |
N2 | 0.9042 (10) | 0.68157 (17) | 0.89778 (14) | 0.0328 (9) | |
N3 | 0.4654 (11) | 0.4802 (2) | 0.8693 (2) | 0.0440 (14) | |
N4 | 0.5816 (11) | 0.52549 (17) | 0.92827 (14) | 0.0335 (10) | |
H4C | 0.6739 | 0.5516 | 0.9399 | 0.040* | |
N5 | 0.6689 (9) | 0.58898 (18) | 0.82977 (14) | 0.0358 (10) | |
H5A | 0.5221 | 0.5756 | 0.8126 | 0.043* | |
N6 | 0.2924 (9) | 0.96564 (16) | 0.66822 (14) | 0.0331 (9) | |
H6 | 0.2014 | 0.9727 | 0.6917 | 0.040* | |
N7 | 0.4102 (10) | 0.93178 (19) | 0.60369 (13) | 0.0339 (10) | |
N8 | −0.0049 (8) | 0.72676 (16) | 0.62888 (15) | 0.0219 (9) | |
N9 | 0.1044 (9) | 0.77626 (19) | 0.57090 (14) | 0.0344 (10) | |
H9 | 0.2124 | 0.7953 | 0.5544 | 0.041* | |
N10 | 0.1853 (9) | 0.83765 (18) | 0.66937 (14) | 0.0362 (10) | |
H10 | 0.1795 | 0.8287 | 0.6955 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.023 (3) | 0.011 (2) | 0.064 (4) | 0.0040 (17) | 0.007 (2) | −0.006 (3) |
C2 | 0.052 (4) | 0.029 (3) | 0.052 (3) | 0.001 (3) | 0.005 (3) | 0.002 (3) |
C3 | 0.044 (3) | 0.032 (3) | 0.069 (4) | −0.010 (2) | 0.013 (3) | −0.010 (3) |
C4 | 0.049 (3) | 0.035 (3) | 0.053 (4) | −0.006 (3) | −0.001 (3) | −0.014 (3) |
C5 | 0.038 (3) | 0.053 (3) | 0.048 (3) | 0.006 (3) | −0.005 (3) | −0.019 (3) |
C6 | 0.036 (3) | 0.029 (3) | 0.025 (3) | 0.003 (2) | −0.007 (2) | 0.002 (2) |
C7 | 0.032 (3) | 0.029 (3) | 0.027 (2) | 0.005 (2) | 0.000 (2) | 0.0004 (19) |
C8 | 0.024 (2) | 0.029 (3) | 0.037 (3) | 0.001 (2) | −0.001 (2) | 0.004 (3) |
C9 | 0.031 (3) | 0.038 (3) | 0.041 (3) | 0.000 (2) | 0.008 (2) | 0.002 (2) |
C10 | 0.030 (3) | 0.032 (3) | 0.037 (3) | 0.004 (2) | 0.000 (2) | 0.000 (2) |
C11 | 0.032 (3) | 0.026 (2) | 0.032 (2) | 0.004 (2) | 0.001 (2) | 0.002 (2) |
C12 | 0.048 (3) | 0.029 (3) | 0.048 (3) | −0.009 (2) | 0.004 (3) | −0.008 (3) |
C13 | 0.053 (4) | 0.043 (4) | 0.052 (4) | −0.009 (3) | 0.015 (3) | 0.006 (4) |
C14 | 0.066 (4) | 0.050 (4) | 0.046 (4) | −0.018 (3) | 0.027 (3) | 0.009 (3) |
C15 | 0.062 (4) | 0.061 (4) | 0.028 (3) | 0.002 (3) | 0.003 (3) | −0.002 (3) |
C16 | 0.031 (3) | 0.034 (3) | 0.039 (3) | −0.001 (2) | 0.006 (2) | 0.002 (2) |
C17 | 0.033 (3) | 0.041 (4) | 0.047 (4) | −0.002 (2) | 0.004 (3) | 0.001 (3) |
C18 | 0.029 (3) | 0.034 (3) | 0.035 (3) | 0.006 (2) | −0.008 (2) | −0.003 (2) |
C19 | 0.045 (3) | 0.050 (4) | 0.010 (2) | 0.005 (2) | −0.0058 (18) | 0.000 (2) |
C20 | 0.050 (3) | 0.039 (3) | 0.041 (3) | 0.004 (3) | −0.010 (3) | −0.003 (3) |
C21 | 0.052 (4) | 0.038 (3) | 0.060 (4) | −0.004 (3) | −0.019 (3) | 0.001 (3) |
C22 | 0.034 (3) | 0.055 (4) | 0.061 (4) | −0.005 (3) | −0.011 (3) | 0.025 (3) |
C23 | 0.041 (3) | 0.045 (3) | 0.034 (3) | 0.002 (3) | −0.002 (2) | 0.006 (2) |
C24 | 0.024 (2) | 0.036 (3) | 0.035 (3) | 0.002 (2) | −0.013 (2) | 0.011 (2) |
C25 | 0.032 (3) | 0.035 (3) | 0.049 (3) | −0.002 (2) | −0.008 (2) | 0.002 (2) |
C26 | 0.027 (3) | 0.029 (3) | 0.039 (3) | 0.005 (2) | 0.002 (2) | −0.003 (2) |
C27 | 0.027 (2) | 0.025 (2) | 0.031 (2) | 0.0003 (19) | 0.000 (2) | 0.002 (2) |
C28 | 0.037 (3) | 0.030 (3) | 0.048 (3) | −0.006 (2) | 0.004 (2) | 0.001 (2) |
C29 | 0.039 (4) | 0.033 (4) | 0.059 (5) | −0.006 (2) | −0.007 (3) | −0.005 (4) |
C30 | 0.046 (3) | 0.058 (4) | 0.046 (4) | 0.003 (3) | −0.008 (3) | −0.008 (3) |
C31 | 0.047 (3) | 0.047 (3) | 0.036 (3) | −0.012 (3) | −0.002 (3) | −0.001 (3) |
C32 | 0.036 (3) | 0.022 (2) | 0.034 (3) | 0.000 (2) | 0.005 (2) | 0.001 (2) |
O1 | 0.055 (3) | 0.061 (3) | 0.032 (2) | −0.005 (2) | 0.0010 (18) | −0.012 (2) |
O2 | 0.078 (3) | 0.046 (3) | 0.066 (3) | −0.001 (2) | 0.021 (3) | 0.004 (2) |
O3 | 0.057 (3) | 0.070 (3) | 0.053 (3) | −0.006 (2) | 0.000 (2) | 0.017 (3) |
O4 | 0.060 (3) | 0.081 (4) | 0.054 (3) | 0.005 (3) | −0.016 (2) | 0.001 (3) |
O5 | 0.067 (3) | 0.061 (3) | 0.057 (3) | −0.001 (3) | −0.014 (2) | −0.006 (2) |
O6 | 0.064 (3) | 0.033 (2) | 0.034 (2) | −0.0043 (17) | −0.0004 (18) | −0.0065 (18) |
O7 | 0.047 (2) | 0.054 (2) | 0.037 (2) | −0.0138 (19) | −0.0022 (17) | 0.0034 (18) |
O8 | 0.051 (2) | 0.047 (2) | 0.038 (2) | −0.0120 (18) | 0.0026 (18) | −0.0016 (18) |
N1 | 0.043 (3) | 0.033 (2) | 0.027 (2) | 0.0043 (19) | −0.0049 (19) | −0.0013 (18) |
N2 | 0.037 (2) | 0.030 (2) | 0.032 (2) | −0.001 (2) | 0.000 (2) | 0.0005 (18) |
N3 | 0.039 (3) | 0.046 (3) | 0.047 (3) | 0.004 (2) | −0.002 (2) | 0.008 (3) |
N4 | 0.044 (3) | 0.026 (2) | 0.030 (2) | −0.009 (2) | −0.0025 (19) | −0.0042 (18) |
N5 | 0.038 (2) | 0.040 (2) | 0.029 (2) | −0.005 (2) | 0.0014 (19) | 0.0004 (19) |
N6 | 0.035 (2) | 0.035 (2) | 0.029 (2) | 0.0026 (19) | −0.0027 (18) | −0.0019 (18) |
N7 | 0.033 (2) | 0.041 (3) | 0.027 (2) | 0.006 (2) | −0.0018 (19) | −0.0052 (19) |
N8 | 0.031 (2) | 0.014 (2) | 0.021 (2) | −0.0017 (14) | −0.0015 (14) | 0.0053 (18) |
N9 | 0.028 (2) | 0.040 (3) | 0.035 (2) | −0.009 (2) | −0.0002 (19) | 0.005 (2) |
N10 | 0.039 (2) | 0.040 (3) | 0.030 (2) | −0.004 (2) | −0.0041 (19) | 0.0031 (19) |
Geometric parameters (Å, º) top
C1—N1 | 1.375 (7) | C21—C22 | 1.411 (10) |
C1—C2 | 1.384 (8) | C21—H21 | 0.9300 |
C1—C6 | 1.410 (9) | C22—C23 | 1.362 (9) |
C2—C3 | 1.371 (9) | C22—H22 | 0.9300 |
C2—H2 | 0.9300 | C23—C24 | 1.384 (8) |
C3—C4 | 1.392 (10) | C23—H23 | 0.9300 |
C3—H3 | 0.9300 | C24—N7 | 1.384 (7) |
C4—C5 | 1.399 (9) | C25—N10 | 1.464 (7) |
C4—H4 | 0.9300 | C25—C26 | 1.501 (7) |
C5—C6 | 1.398 (8) | C25—H25A | 0.9700 |
C5—H5 | 0.9300 | C25—H25B | 0.9700 |
C6—N2 | 1.390 (7) | C26—N8 | 1.334 (6) |
C7—N2 | 1.322 (6) | C26—N9 | 1.351 (7) |
C7—N1 | 1.361 (6) | C27—N8 | 1.364 (7) |
C7—C8 | 1.476 (7) | C27—C28 | 1.387 (7) |
C8—N5 | 1.476 (7) | C27—C32 | 1.397 (7) |
C8—H8A | 0.9700 | C28—C29 | 1.348 (9) |
C8—H8B | 0.9700 | C28—H28 | 0.9300 |
C9—N5 | 1.475 (7) | C29—C30 | 1.428 (10) |
C9—C10 | 1.492 (7) | C29—H29 | 0.9300 |
C9—H9A | 0.9700 | C30—C31 | 1.387 (9) |
C9—H9B | 0.9700 | C30—H30 | 0.9300 |
C10—N3 | 1.280 (7) | C31—C32 | 1.403 (8) |
C10—N4 | 1.362 (7) | C31—H31 | 0.9300 |
C11—C12 | 1.387 (7) | C32—N9 | 1.366 (7) |
C11—C16 | 1.404 (7) | O1—H1A | 0.8253 |
C11—N3 | 1.418 (8) | O1—H1B | 0.8206 |
C12—C13 | 1.395 (9) | O2—H2A | 0.8256 |
C12—H12 | 0.9300 | O2—H2B | 0.8257 |
C13—C14 | 1.329 (11) | O3—H3A | 0.8246 |
C13—H13 | 0.9300 | O3—H3B | 0.8259 |
C14—C15 | 1.370 (9) | O4—H4A | 0.8260 |
C14—H14 | 0.9300 | O4—H4B | 0.8150 |
C15—C16 | 1.398 (8) | O5—H5B | 0.8284 |
C15—H15 | 0.9300 | O5—H5C | 0.8254 |
C16—N4 | 1.373 (7) | O6—H6A | 0.8219 |
C17—N10 | 1.454 (8) | O6—H6B | 0.8228 |
C17—C18 | 1.483 (8) | O7—H7A | 0.8251 |
C17—H17A | 0.9700 | O7—H7B | 0.8227 |
C17—H17B | 0.9700 | O8—H8C | 0.8222 |
C18—N7 | 1.317 (7) | O8—H8D | 0.8244 |
C18—N6 | 1.351 (7) | N1—H1 | 0.8594 |
C19—N6 | 1.378 (8) | N4—H4C | 0.8589 |
C19—C24 | 1.384 (8) | N5—H5A | 0.9311 |
C19—C20 | 1.391 (9) | N6—H6 | 0.8597 |
C20—C21 | 1.365 (9) | N9—H9 | 0.8602 |
C20—H20 | 0.9300 | N10—H10 | 0.8363 |
| | | |
N1—C1—C2 | 132.4 (6) | C20—C21—C22 | 120.6 (6) |
N1—C1—C6 | 103.9 (5) | C20—C21—H21 | 119.7 |
C2—C1—C6 | 123.7 (5) | C22—C21—H21 | 119.7 |
C3—C2—C1 | 115.9 (6) | C23—C22—C21 | 121.6 (6) |
C3—C2—H2 | 122.1 | C23—C22—H22 | 119.2 |
C1—C2—H2 | 122.1 | C21—C22—H22 | 119.2 |
C2—C3—C4 | 123.4 (6) | C22—C23—C24 | 117.9 (6) |
C2—C3—H3 | 118.3 | C22—C23—H23 | 121.0 |
C4—C3—H3 | 118.3 | C24—C23—H23 | 121.0 |
C3—C4—C5 | 119.9 (6) | N7—C24—C23 | 130.1 (5) |
C3—C4—H4 | 120.1 | N7—C24—C19 | 109.3 (5) |
C5—C4—H4 | 120.1 | C23—C24—C19 | 120.6 (5) |
C6—C5—C4 | 118.8 (6) | N10—C25—C26 | 111.9 (4) |
C6—C5—H5 | 120.6 | N10—C25—H25A | 109.2 |
C4—C5—H5 | 120.6 | C26—C25—H25A | 109.2 |
N2—C6—C5 | 131.4 (5) | N10—C25—H25B | 109.2 |
N2—C6—C1 | 110.2 (4) | C26—C25—H25B | 109.2 |
C5—C6—C1 | 118.4 (5) | H25A—C25—H25B | 107.9 |
N2—C7—N1 | 111.7 (4) | N8—C26—N9 | 112.3 (5) |
N2—C7—C8 | 127.2 (5) | N8—C26—C25 | 123.5 (5) |
N1—C7—C8 | 121.0 (5) | N9—C26—C25 | 124.1 (5) |
C7—C8—N5 | 110.3 (4) | N8—C27—C28 | 129.2 (5) |
C7—C8—H8A | 109.6 | N8—C27—C32 | 109.9 (4) |
N5—C8—H8A | 109.6 | C28—C27—C32 | 120.8 (5) |
C7—C8—H8B | 109.6 | C29—C28—C27 | 119.2 (5) |
N5—C8—H8B | 109.6 | C29—C28—H28 | 120.4 |
H8A—C8—H8B | 108.1 | C27—C28—H28 | 120.4 |
N5—C9—C10 | 113.7 (4) | C28—C29—C30 | 121.2 (5) |
N5—C9—H9A | 108.8 | C28—C29—H29 | 119.4 |
C10—C9—H9A | 108.8 | C30—C29—H29 | 119.4 |
N5—C9—H9B | 108.8 | C31—C30—C29 | 120.2 (6) |
C10—C9—H9B | 108.8 | C31—C30—H30 | 119.9 |
H9A—C9—H9B | 107.7 | C29—C30—H30 | 119.9 |
N3—C10—N4 | 113.1 (5) | C30—C31—C32 | 117.8 (5) |
N3—C10—C9 | 123.0 (5) | C30—C31—H31 | 121.1 |
N4—C10—C9 | 123.5 (5) | C32—C31—H31 | 121.1 |
C12—C11—C16 | 120.4 (5) | N9—C32—C27 | 105.6 (4) |
C12—C11—N3 | 131.1 (5) | N9—C32—C31 | 133.6 (5) |
C16—C11—N3 | 108.5 (5) | C27—C32—C31 | 120.7 (5) |
C11—C12—C13 | 115.9 (5) | H1A—O1—H1B | 110.4 |
C11—C12—H12 | 122.1 | H2A—O2—H2B | 109.1 |
C13—C12—H12 | 122.1 | H3A—O3—H3B | 109.7 |
C14—C13—C12 | 122.9 (6) | H4A—O4—H4B | 110.4 |
C14—C13—H13 | 118.5 | H5B—O5—H5C | 109.0 |
C12—C13—H13 | 118.5 | H6A—O6—H6B | 110.1 |
C13—C14—C15 | 123.5 (6) | H7A—O7—H7B | 109.8 |
C13—C14—H14 | 118.2 | H8C—O8—H8D | 110.2 |
C15—C14—H14 | 118.2 | C7—N1—C1 | 108.9 (5) |
C14—C15—C16 | 115.3 (6) | C7—N1—H1 | 122.5 |
C14—C15—H15 | 122.3 | C1—N1—H1 | 128.5 |
C16—C15—H15 | 122.3 | C7—N2—C6 | 105.3 (4) |
N4—C16—C15 | 133.2 (5) | C10—N3—C11 | 105.6 (5) |
N4—C16—C11 | 104.9 (4) | C10—N4—C16 | 107.8 (4) |
C15—C16—C11 | 121.9 (5) | C10—N4—H4C | 116.7 |
N10—C17—C18 | 111.9 (5) | C16—N4—H4C | 135.6 |
N10—C17—H17A | 109.2 | C9—N5—C8 | 113.2 (4) |
C18—C17—H17A | 109.2 | C9—N5—H5A | 117.4 |
N10—C17—H17B | 109.2 | C8—N5—H5A | 103.6 |
C18—C17—H17B | 109.2 | C18—N6—C19 | 106.1 (5) |
H17A—C17—H17B | 107.9 | C18—N6—H6 | 130.1 |
N7—C18—N6 | 113.4 (5) | C19—N6—H6 | 123.4 |
N7—C18—C17 | 125.6 (5) | C18—N7—C24 | 104.9 (4) |
N6—C18—C17 | 120.9 (5) | C26—N8—C27 | 105.0 (4) |
N6—C19—C24 | 106.3 (5) | C26—N9—C32 | 107.1 (4) |
N6—C19—C20 | 132.0 (5) | C26—N9—H9 | 124.7 |
C24—C19—C20 | 121.7 (6) | C32—N9—H9 | 126.6 |
C21—C20—C19 | 117.6 (6) | C17—N10—C25 | 114.6 (5) |
C21—C20—H20 | 121.2 | C17—N10—H10 | 130.3 |
C19—C20—H20 | 121.2 | C25—N10—H10 | 114.9 |
| | | |
N1—C1—C2—C3 | −178.4 (5) | C28—C29—C30—C31 | −3.2 (10) |
C6—C1—C2—C3 | 1.1 (8) | C29—C30—C31—C32 | 2.3 (9) |
C1—C2—C3—C4 | 1.4 (9) | N8—C27—C32—N9 | 0.4 (6) |
C2—C3—C4—C5 | −2.7 (9) | C28—C27—C32—N9 | −180.0 (5) |
C3—C4—C5—C6 | 1.5 (9) | N8—C27—C32—C31 | 178.3 (5) |
C4—C5—C6—N2 | 176.9 (5) | C28—C27—C32—C31 | −2.0 (8) |
C4—C5—C6—C1 | 0.8 (8) | C30—C31—C32—N9 | 177.5 (6) |
N1—C1—C6—N2 | 0.6 (6) | C30—C31—C32—C27 | 0.2 (8) |
C2—C1—C6—N2 | −179.0 (5) | N2—C7—N1—C1 | −0.8 (6) |
N1—C1—C6—C5 | 177.4 (5) | C8—C7—N1—C1 | −178.8 (4) |
C2—C1—C6—C5 | −2.2 (8) | C2—C1—N1—C7 | 179.6 (6) |
N2—C7—C8—N5 | −92.7 (6) | C6—C1—N1—C7 | 0.1 (5) |
N1—C7—C8—N5 | 85.1 (6) | N1—C7—N2—C6 | 1.1 (6) |
N5—C9—C10—N3 | 69.8 (7) | C8—C7—N2—C6 | 179.0 (5) |
N5—C9—C10—N4 | −103.5 (6) | C5—C6—N2—C7 | −177.4 (6) |
C16—C11—C12—C13 | −0.6 (8) | C1—C6—N2—C7 | −1.0 (6) |
N3—C11—C12—C13 | −179.3 (6) | N4—C10—N3—C11 | −4.2 (6) |
C11—C12—C13—C14 | 2.4 (10) | C9—C10—N3—C11 | −178.1 (5) |
C12—C13—C14—C15 | −3.3 (12) | C12—C11—N3—C10 | −178.8 (5) |
C13—C14—C15—C16 | 2.0 (11) | C16—C11—N3—C10 | 2.5 (6) |
C14—C15—C16—N4 | 177.8 (6) | N3—C10—N4—C16 | 4.4 (7) |
C14—C15—C16—C11 | −0.2 (9) | C9—C10—N4—C16 | 178.2 (5) |
C12—C11—C16—N4 | −178.9 (5) | C15—C16—N4—C10 | 179.3 (6) |
N3—C11—C16—N4 | 0.1 (6) | C11—C16—N4—C10 | −2.5 (6) |
C12—C11—C16—C15 | −0.4 (8) | C10—C9—N5—C8 | 70.3 (6) |
N3—C11—C16—C15 | 178.5 (5) | C7—C8—N5—C9 | 83.4 (5) |
N10—C17—C18—N7 | 88.8 (7) | N7—C18—N6—C19 | 0.2 (6) |
N10—C17—C18—N6 | −86.7 (6) | C17—C18—N6—C19 | 176.3 (5) |
N6—C19—C20—C21 | 179.7 (6) | C24—C19—N6—C18 | −0.7 (6) |
C24—C19—C20—C21 | −2.5 (8) | C20—C19—N6—C18 | 177.3 (6) |
C19—C20—C21—C22 | 1.9 (9) | N6—C18—N7—C24 | 0.3 (6) |
C20—C21—C22—C23 | −0.4 (9) | C17—C18—N7—C24 | −175.5 (5) |
C21—C22—C23—C24 | −0.8 (8) | C23—C24—N7—C18 | −179.4 (5) |
C22—C23—C24—N7 | 178.7 (5) | C19—C24—N7—C18 | −0.8 (6) |
C22—C23—C24—C19 | 0.2 (8) | N9—C26—N8—C27 | −1.2 (6) |
N6—C19—C24—N7 | 1.0 (6) | C25—C26—N8—C27 | 176.1 (5) |
C20—C19—C24—N7 | −177.3 (5) | C28—C27—N8—C26 | −179.2 (5) |
N6—C19—C24—C23 | 179.7 (5) | C32—C27—N8—C26 | 0.5 (5) |
C20—C19—C24—C23 | 1.4 (8) | N8—C26—N9—C32 | 1.4 (6) |
N10—C25—C26—N8 | −73.2 (6) | C25—C26—N9—C32 | −175.8 (5) |
N10—C25—C26—N9 | 103.8 (6) | C27—C32—N9—C26 | −1.0 (6) |
N8—C27—C28—C29 | −179.2 (5) | C31—C32—N9—C26 | −178.6 (6) |
C32—C27—C28—C29 | 1.2 (8) | C18—C17—N10—C25 | −82.2 (6) |
C27—C28—C29—C30 | 1.4 (9) | C26—C25—N10—C17 | −70.9 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O6 | 0.82 | 2.10 | 2.789 (7) | 142 |
O2—H2A···O6 | 0.83 | 2.49 | 2.795 (7) | 103 |
O2—H2B···O3 | 0.83 | 2.18 | 2.895 (7) | 145 |
O3—H3B···N8 | 0.83 | 2.00 | 2.782 (7) | 157 |
O4—H4A···O5 | 0.83 | 2.16 | 2.788 (8) | 133 |
O4—H4B···N1 | 0.82 | 2.24 | 2.823 (7) | 128 |
O5—H5B···N10 | 0.83 | 2.04 | 2.853 (6) | 169 |
O6—H6A···O2 | 0.82 | 2.01 | 2.795 (7) | 159 |
O6—H6B···O1 | 0.82 | 1.97 | 2.789 (7) | 176 |
O7—H7B···N2 | 0.82 | 2.01 | 2.828 (6) | 173 |
O8—H8C···N7 | 0.82 | 2.09 | 2.858 (6) | 155 |
N1—H1···O4 | 0.86 | 1.98 | 2.823 (7) | 166 |
N4—H4C···O7 | 0.86 | 2.09 | 2.939 (6) | 171 |
N5—H5A···O2 | 0.93 | 2.57 | 3.387 (7) | 148 |
N6—H6···O6i | 0.86 | 2.02 | 2.875 (6) | 175 |
N9—H9···O8 | 0.86 | 2.12 | 2.913 (6) | 153 |
N10—H10···O5 | 0.84 | 2.40 | 2.853 (6) | 114 |
O1—H1A···O6ii | 0.83 | 2.01 | 2.823 (6) | 169 |
O3—H3A···O4iii | 0.82 | 2.09 | 2.807 (7) | 145 |
O5—H5C···O1iv | 0.83 | 2.11 | 2.877 (7) | 155 |
O7—H7A···O8v | 0.83 | 2.09 | 2.903 (6) | 168 |
O8—H8D···O7vi | 0.82 | 2.10 | 2.886 (6) | 160 |
C8—H8B···Cg1iii | 0.97 | 2.85 | 3.545 (1) | 129 |
C17—H17A···Cg2iii | 0.97 | 2.95 | 3.612 (1) | 127 |
Symmetry codes: (i) −x, y+1/2, z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+1, y+1/2, z; (v) x+1, −y+3/2, z+1/2; (vi) x, −y+3/2, z−1/2. |